US7582325B2 - Process for the preparation of tomato extracts with high content in lycopene - Google Patents
Process for the preparation of tomato extracts with high content in lycopene Download PDFInfo
- Publication number
- US7582325B2 US7582325B2 US10/509,062 US50906205A US7582325B2 US 7582325 B2 US7582325 B2 US 7582325B2 US 50906205 A US50906205 A US 50906205A US 7582325 B2 US7582325 B2 US 7582325B2
- Authority
- US
- United States
- Prior art keywords
- lycopene
- concentrate
- ethyl acetate
- water
- extract
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime, expires
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
- A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
Definitions
- the present invention relates to a process for the preparation of tomato extracts with high content in lycopene.
- Lycopene is a natural pigment, particularly abundant in tomatoes and watermelon, having intense red color. Due to this characteristic, as well as its safety and beneficial effects, lycopene is widely used in the food industry as a coloring agent, usually in the form of oleoresin, i.e. a suspension in natural lipids. In this form, lycopene oxidation (crystalline lycopene being highly unstable) and bacterial degradation are prevented, most likely due to the lipids and natural antioxidants present. Furthermore, lycopene is used as food supplement thanks to its antioxidative and chemoprotective properties.
- lycopene can be prepared by synthesis [Karrer et al., Helv. Chim. Acta 33, 1349 (1950); Isler et al., ibid. 39, 463 (1956)], it is usually obtained by extraction from tomatoes ( Lycopersicum esculentum ). As lycopene has intense red color only when in the crystalline form, the extraction process should allow to obtain the product in this form.
- the lycopene starting content should preferably be above 50 ppm.
- the present invention relates to a process for the preparation of tomato whole extracts with lycopene content from 5% to 20% and with reducing sugars content, expressed as glucose, below 1%, which process comprises the following steps:
- pretreating fresh tomatoes which comprises washing, then cutting or crushing
- step c) extracting the concentrate from step b) with water-saturated ethyl acetate;
- Pre-treatment is carried out according to conventional techniques and any method providing a homogeneous cut/crushed tomato will be suitable.
- step b is carried out by distillation under reduced pressure, at temperatures ranging from 40 to 70° C., preferably at 50° C., so that the weight of the cut/crushed tomato will be 20-30% the starting value.
- Extraction of the concentrate is repeatedly performed with water-saturated ethyl acetate in a volume ranging from 1.0 to 2.5, preferably 2, times the weight of the concentrate, to obtain a lycopene-free residue.
- the extraction is repeated four times. The extraction is carried out for at least one hour at room temperature, shielding from light and keeping the concentrate-solvent mixture under stirring.
- step d Each extract is washed with water (step d), preferably in half the volume of the solvent used for each single extraction, after that the extracts are combined, filtered and evaporated to dryness under reduced pressure (step e). Washing with water is mandatory for the success of the process; it has in fact been observed that, when this step is omitted, as illustrated in detail in the subsequent example 3, a higher amount of whole extract is obtained which has however percent lycopene content lower by about one third (approximately 4% instead of 6%, for tomatoes containing 50 ppm of lycopene).
- the process of the invention allows to obtain crystalline lycopene, with purity higher than 50%, from which the oleoresin can be prepared.
- steps a)-d) are carried out as described above, whereas at step e) the extract is concentrated to a final volume ranging from 0.10 to 0.28% with respect to the starting volume.
- the concentrated extract is then left to stand for some hours and the lycopene crystalline precipitate is filtered off and dried (step f).
- the resulting crystalline lycopene may optionally be suspended in ethanol, then filtered and washed with ethyl acetate until obtaining the desired purity.
- the oleoresin is obtained by adding seed oil to the lycopene crystals, preferably tomato seed oil or soybean oil (step g).
- the process according to the present invention provides good yields even when using tomatoes with low starting content in lycopene and it allows to obtain a whole extract with high lycopene content, ranging from 5% to 20%, which is about twice higher that obtained with the method disclosed in WO 97/48287, as illustrated in the Comparison Example below.
- This process is also advantageous in that the reducing sugars content in the extract is always lower than 1%, usually lower than 0.5%.
- Part of water (34 L) is distilled off under reduced pressure (20 mBar) at 60° C. and discarded, to obtain 17.8 Kg of tomato concentrate.
- Part of water (31 L) is distilled off under reduced pressure (20 mBar) at 60° C. and discarded, to obtain 18.8 Kg of tomato concentrate.
- Tomatoes belonging to the same lot as in Example 1, with lycopene content of 50 ppm, are used.
- the resulting concentrate (1.17 kg) is extracted 4 times with 2.3 L each of (9.2 L of solvent totally), stirring each time for 2 hours at room temperature and shielding from light.
- the extracts are combined, filtered and concentrated to dryness under reduced pressure.
- the resulting whole extract (5.09 g) has HPLC lycopene content of 4%, reducing sugars content (expressed as glucose) of 4.46%, phospholipids content of 16.51% and a mono-di-glycerids content of 14.47%.
- Example 2 The procedure of Example 1 is followed, but concentrating the combined extracts to 200 ml final volume. The concentrated extract is left to stand overnight, shielded from light, to obtain a dark red needle crystal, which is filtered under vacuum, shielding from air, washed with ethyl acetate and dried under vacuum at 50° C., to obtain 4.23 g of crystalline lycopene with 51% purity.
- the crystalline lycopene is added with 6.75 g of tomato seed oil (obtained by hexane extraction) and the mixture is stirred vigorously, to obtain 10.7 g of a fluid, homogeneous, dark red product having 19.8% lycopene content.
- Example 2 The procedure of Example 1 is followed, but concentrating the combined extracts to a final volume of 200 ml.
- the concentrated extract is left to stand overnight, shielded from light, to obtain a dark red needle crystal, which is filtered under vacuum, shielding from air, washed with ethyl acetate and dried under vacuum at 50° C., to obtain 4.23 g of crystalline lycopene with 51% purity.
- the crystalline lycopene is added with 6.75 g of soybean oil (obtained by hexane extraction) and the mixture is stirred vigorously, to obtain 10.7 g of a fluid, homogeneous, dark red product having 19.8% lycopene content.
- Example 1 The procedure of Example 1 is followed, but concentrating the combined extracts to a final volume of 200 ml.
- the concentrated extract is left to stand overnight, shielded from light, to obtain a dark red needle crystal, which is filtered under vacuum, shielding from air.
- the solid is suspended in 80 ml of ethyl acetate and heated to 45° C. with stirring for 20 min. The mixture is then left to cool to room temperature and filtered under vacuum, shielding from air.
- the solid is suspended in 200 ml of ethanol and heated to 45° C. with stirring for 10 min, then filtered while hot, under vacuum and shielding from air. This procedure is repeated once more. After that, the solid is washed on the filter with 40 ml of cold ethyl acetate, then dried under vacuum at 50° C., to obtain 2.05 g of crystalline lycopene with 95% purity.
- Tomatoes belonging to the same lot as in Example 1, with lycopene content of 50 ppm, are used.
- the extracts are combined and concentrated to dryness under reduced pressure.
- the resulting tomato whole extract (6.07 g) has HPLC lycopene content of 3.5%, reducing sugars content (expressed as glucose) of 8.74%, phospholipids content of 35.57% and mono-di-glycerids content of 12.44%.
Landscapes
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines Containing Plant Substances (AREA)
- Preparation Of Fruits And Vegetables (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2002A000632 | 2002-03-27 | ||
| IT2002MI000632A ITMI20020632A1 (it) | 2002-03-27 | 2002-03-27 | Processo per la preparazione di estratti di pomodoro ad elevato contenuto di licopene |
| ITMI2002A0632 | 2002-03-27 | ||
| PCT/EP2003/002749 WO2003079816A1 (en) | 2002-03-27 | 2003-03-17 | A process for the preparation of tomato extracts with high content in lycopene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| US20050153038A1 US20050153038A1 (en) | 2005-07-14 |
| US7582325B2 true US7582325B2 (en) | 2009-09-01 |
Family
ID=11449581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/509,062 Expired - Lifetime US7582325B2 (en) | 2002-03-27 | 2003-03-17 | Process for the preparation of tomato extracts with high content in lycopene |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7582325B2 (de) |
| EP (1) | EP1487282B1 (de) |
| JP (1) | JP4276088B2 (de) |
| KR (1) | KR101037271B1 (de) |
| CN (1) | CN1323610C (de) |
| AT (1) | ATE326865T1 (de) |
| AU (1) | AU2003218777B2 (de) |
| CA (1) | CA2480337C (de) |
| DE (2) | DE10246770A1 (de) |
| DK (1) | DK1487282T3 (de) |
| ES (1) | ES2263961T3 (de) |
| IL (1) | IL164253A0 (de) |
| IT (1) | ITMI20020632A1 (de) |
| NO (1) | NO326876B1 (de) |
| PL (1) | PL203697B1 (de) |
| PT (1) | PT1487282E (de) |
| RU (1) | RU2304886C2 (de) |
| WO (1) | WO2003079816A1 (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100190867A1 (en) * | 2006-08-08 | 2010-07-29 | Indena S.P.A. | Stable and bioavailable compositions of isomers of lycopene for skin and hair |
| WO2016204544A1 (ko) * | 2015-06-17 | 2016-12-22 | 주식회사 조은푸드텍 | 식물체로부터 라이코펜을 효율적으로 추출하는 방법 |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040166177A1 (en) * | 2002-09-12 | 2004-08-26 | Martin Michael Z. | Full range nutritional supplements from plant materials and methods for their manufacture |
| EP1716210B1 (de) * | 2004-02-10 | 2016-10-05 | Nestec S.A. | Zusammensetzungen mit cis-isomeren von carotinoiden und entsprechendes verfahren |
| ES2283164B1 (es) * | 2004-06-09 | 2008-12-16 | Consejo Sup. Investig. Cientificas | Obtencion de todo-trans-licopeno utilizando disolventes de grado alimentario a baja temperatura. |
| EP1676888B1 (de) * | 2004-11-05 | 2012-10-24 | Conservas Vegetales de Extremadura, S.A. | Verfahren zur gewinnung von lycopin aus tomatenhäuten und -kernen |
| US9579298B2 (en) | 2004-12-02 | 2017-02-28 | Piotr Chomczynski | Antioxidant dietary supplement compositions and methods for maintaining healthy skin |
| ES2241503B2 (es) * | 2005-04-19 | 2008-07-01 | Eduardo Sabio Rey | Procedimiento para preparar formulaciones enriquecidas en licopeno libres de disolventes organicos, formulaciones obtenidas, composiciones que comprenden dichas formulaciones y uso de las mismas. |
| KR100692253B1 (ko) * | 2005-04-26 | 2007-03-09 | 충북대학교 산학협력단 | 토마토로부터 리코펜을 직접 추출하는 방법 |
| GB0610790D0 (en) * | 2006-06-02 | 2006-07-12 | Provexis Natural Products Ltd | Therapeutic uses of tomato extracts |
| US8216619B2 (en) * | 2006-08-08 | 2012-07-10 | Indena S.P.A. | Stable and bioavailable compositions of isomers of carotenoids for skin and hair |
| ITRM20060602A1 (it) * | 2006-11-07 | 2008-05-08 | E One S R L | Procedimento per l estrazione di licopene dai cascami del pomodoro |
| US7642062B2 (en) | 2006-12-29 | 2010-01-05 | Avon Products Inc. | Compositions and methods of their use for improving the condition and appearance of skin |
| KR100845317B1 (ko) * | 2007-01-23 | 2008-07-10 | 한국식품연구원 | 마이크로이멀젼 기법에 의한 라이코펜 회수 및 수용화 |
| KR100903840B1 (ko) * | 2007-08-14 | 2009-06-25 | 진주산업대학교 산학협력단 | 고함량의 토마토 라이코펜 소재물의 제조방법 및 용도 |
| GB0819959D0 (en) | 2008-10-31 | 2008-12-10 | Provexis Natural Products Ltd | Fruit extracts |
| GB0819958D0 (en) * | 2008-10-31 | 2008-12-10 | Provexis Natural Products Ltd | Therapeutic compositions |
| CN101928473B (zh) * | 2009-06-22 | 2013-09-25 | 新疆大学 | 一种生产番茄红素油树脂的方法 |
| CN101779779A (zh) * | 2010-04-14 | 2010-07-21 | 杜为民 | 一种提高番茄加工制品中番茄红素含量的加工工艺 |
| WO2012002950A1 (en) | 2010-06-30 | 2012-01-05 | Avon Products, Inc. | Use of tiliacora triandra in cosmetics and compositions thereof |
| EP2588593B1 (de) | 2010-06-30 | 2017-08-23 | Avon Products, Inc. | Zusammensetzungen und verfahren zur magp-1-stimulation zur verbesserung des erscheinungsbildes der haut |
| MX380274B (es) | 2011-06-30 | 2025-03-12 | Gallo Winery E & J | Colorante cristalino natural y proceso para producción. |
| AU2015202392B2 (en) * | 2011-06-30 | 2016-09-01 | E. & J. Gallo Winery | Natural crystalline colorant and process for production |
| CA2848955A1 (en) * | 2011-09-19 | 2013-03-28 | Omniactive Health Technologies Limited | An efficient process for the preparation of lycopene containing oleoresin and lycopene crystals for human consumption |
| KR101347289B1 (ko) * | 2011-11-30 | 2014-01-10 | 신라대학교 산학협력단 | 토마토 유래 라이코펜 추출방법에 따른 토마토 유래 라이코펜 및 이를 함유한 탈모 방지 및 모발 성장 촉진 효과를 갖는 화장료 조성물 |
| US20150132371A1 (en) | 2012-04-23 | 2015-05-14 | University Of Oslo | Use of tomato extract as antihypertensive agent and process for making water soluble sugar free tomato extract |
| GB201223365D0 (en) | 2012-12-24 | 2013-02-06 | Provexis Natural Products Ltd | Compositions |
| US11226155B2 (en) | 2013-03-15 | 2022-01-18 | E. & J. Gallo Winery | Multi-chamber dryer using adjustable conditioned air flow |
| JP2016119898A (ja) * | 2014-12-16 | 2016-07-07 | ライコード・リミテツド | 着色剤特性が改善されたリコピン組成物 |
| US10905733B2 (en) | 2016-11-02 | 2021-02-02 | Provexis Natural Products Limited | Water soluble tomato extract protects against adverse effects of air pollution |
| KR102081489B1 (ko) * | 2017-11-28 | 2020-02-26 | 신라대학교 산학협력단 | 알카리 가수분해 및 염석결정화를 이용한 토마토로부터 수용성 라이코펜 제조 및 라이코펜 분말 수득방법 |
| WO2019122444A1 (en) * | 2017-12-21 | 2019-06-27 | Dsm Ip Assets B.V. | Process for the manufacture of an extract containing lycopene |
| CN108452082A (zh) * | 2018-05-17 | 2018-08-28 | 金华市飞凌生物科技有限公司 | 一种番茄提取物 |
| US11221179B2 (en) | 2018-10-26 | 2022-01-11 | E. & J. Gallo Winery | Low profile design air tunnel system and method for providing uniform air flow in a refractance window dryer |
| MA62378B1 (fr) | 2023-09-21 | 2025-07-31 | Les Conserves De Meknes | Procédé innovant d’extraction de lycopène naturel, pur et stable utilisant un solvant vert |
| JP7810941B1 (ja) * | 2024-03-15 | 2026-02-04 | 日本製鉄株式会社 | 炭素資源の自然発熱抑制剤、炭素資源の自然発熱抑制剤の製造方法、炭素資源の自然発熱抑制方法、及び炭素資源の貯蔵方法 |
Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3467579A (en) | 1966-08-04 | 1969-09-16 | Farmaceutici Italia | Microbiological process for the production of lycopene |
| WO1995016363A1 (en) | 1993-12-13 | 1995-06-22 | Makhteshim Chemical Works Ltd. | An efficient process for the manufacture of tomato products |
| WO1996013178A1 (en) | 1994-10-31 | 1996-05-09 | Makhteshim Chemical Works, Ltd. | Stable lycopene concentrates and process for their preparation |
| WO1997048287A1 (en) | 1996-06-20 | 1997-12-24 | Lycored Natural Products Industries Ltd. | Industrial processing of tomatoes and lycopene extraction |
| EP0818225A1 (de) | 1996-07-12 | 1998-01-14 | INDENA S.p.A. | Ein Verfahren zur Extraktion von Lycopin und Extrakte die Lycopin enthalten |
| RU2112777C1 (ru) | 1996-05-28 | 1998-06-10 | Акционерное общество открытого типа "Уралбиофарм" | Ликопинсодержащий препарат |
| US5858700A (en) | 1997-04-03 | 1999-01-12 | Kemin Foods, Lc | Process for the isolation and purification of lycopene crystals |
| EP0986963A2 (de) | 1998-09-14 | 2000-03-22 | Basf Aktiengesellschaft | Stabile, pulverförmige Lycopin-Formulierungen, enthaltend Lycopin mit einem Kristallinitätsgrad von grösser 20% |
| EP1103579A1 (de) | 1999-11-23 | 2001-05-30 | Societe Des Produits Nestle S.A. | Verfahren zur Extraktion von Lycopin |
| CN1298904A (zh) | 2000-12-18 | 2001-06-13 | 新疆生命红科技投资开发有限责任公司 | 番茄酱制取结晶番茄红素及/或番茄红素油树脂的方法 |
| EP1201762A1 (de) | 1999-08-12 | 2002-05-02 | Vitatene, S.A. | Verfahren zur herstellung von lykopen |
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| JP2743247B2 (ja) * | 1993-11-29 | 1998-04-22 | カゴメ株式会社 | リコピン油の製造方法 |
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-
2002
- 2002-03-27 IT IT2002MI000632A patent/ITMI20020632A1/it unknown
- 2002-10-07 DE DE10246770A patent/DE10246770A1/de not_active Withdrawn
-
2003
- 2003-03-17 JP JP2003577659A patent/JP4276088B2/ja not_active Expired - Lifetime
- 2003-03-17 AT AT03712033T patent/ATE326865T1/de active
- 2003-03-17 US US10/509,062 patent/US7582325B2/en not_active Expired - Lifetime
- 2003-03-17 KR KR1020047014562A patent/KR101037271B1/ko not_active Expired - Lifetime
- 2003-03-17 PL PL371443A patent/PL203697B1/pl unknown
- 2003-03-17 CA CA2480337A patent/CA2480337C/en not_active Expired - Lifetime
- 2003-03-17 PT PT03712033T patent/PT1487282E/pt unknown
- 2003-03-17 ES ES03712033T patent/ES2263961T3/es not_active Expired - Lifetime
- 2003-03-17 EP EP03712033A patent/EP1487282B1/de not_active Expired - Lifetime
- 2003-03-17 DK DK03712033T patent/DK1487282T3/da active
- 2003-03-17 AU AU2003218777A patent/AU2003218777B2/en not_active Expired
- 2003-03-17 WO PCT/EP2003/002749 patent/WO2003079816A1/en not_active Ceased
- 2003-03-17 DE DE60305459T patent/DE60305459T2/de not_active Expired - Lifetime
- 2003-03-17 RU RU2004128462/13A patent/RU2304886C2/ru active
- 2003-03-17 CN CNB038070006A patent/CN1323610C/zh not_active Expired - Lifetime
- 2003-03-26 IL IL16425303A patent/IL164253A0/xx active IP Right Grant
-
2004
- 2004-09-24 NO NO20044021A patent/NO326876B1/no not_active IP Right Cessation
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3467579A (en) | 1966-08-04 | 1969-09-16 | Farmaceutici Italia | Microbiological process for the production of lycopene |
| WO1995016363A1 (en) | 1993-12-13 | 1995-06-22 | Makhteshim Chemical Works Ltd. | An efficient process for the manufacture of tomato products |
| WO1996013178A1 (en) | 1994-10-31 | 1996-05-09 | Makhteshim Chemical Works, Ltd. | Stable lycopene concentrates and process for their preparation |
| RU2112777C1 (ru) | 1996-05-28 | 1998-06-10 | Акционерное общество открытого типа "Уралбиофарм" | Ликопинсодержащий препарат |
| WO1997048287A1 (en) | 1996-06-20 | 1997-12-24 | Lycored Natural Products Industries Ltd. | Industrial processing of tomatoes and lycopene extraction |
| EP0818225A1 (de) | 1996-07-12 | 1998-01-14 | INDENA S.p.A. | Ein Verfahren zur Extraktion von Lycopin und Extrakte die Lycopin enthalten |
| US5858700A (en) | 1997-04-03 | 1999-01-12 | Kemin Foods, Lc | Process for the isolation and purification of lycopene crystals |
| EP0986963A2 (de) | 1998-09-14 | 2000-03-22 | Basf Aktiengesellschaft | Stabile, pulverförmige Lycopin-Formulierungen, enthaltend Lycopin mit einem Kristallinitätsgrad von grösser 20% |
| EP1201762A1 (de) | 1999-08-12 | 2002-05-02 | Vitatene, S.A. | Verfahren zur herstellung von lykopen |
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| CN1298904A (zh) | 2000-12-18 | 2001-06-13 | 新疆生命红科技投资开发有限责任公司 | 番茄酱制取结晶番茄红素及/或番茄红素油树脂的方法 |
| WO2002072509A1 (de) | 2001-01-26 | 2002-09-19 | Basf Aktiengesellschaft | Thermische isomerisierung von lycopin |
| WO2003038064A2 (en) | 2001-10-29 | 2003-05-08 | Dsm Ip Assets B.V. | Blakeslea trispora producing high yield of lycopene in a suitable medium in the absence of an exogenous carotenogenesis inhibitor |
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| Title |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100190867A1 (en) * | 2006-08-08 | 2010-07-29 | Indena S.P.A. | Stable and bioavailable compositions of isomers of lycopene for skin and hair |
| US8568806B2 (en) * | 2006-08-08 | 2013-10-29 | Indena, S.P.A. | Stable and bioavailable compositions of isomers of lycopene for skin and hair |
| WO2016204544A1 (ko) * | 2015-06-17 | 2016-12-22 | 주식회사 조은푸드텍 | 식물체로부터 라이코펜을 효율적으로 추출하는 방법 |
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| Publication number | Publication date |
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| PL371443A1 (en) | 2005-06-13 |
| RU2004128462A (ru) | 2005-04-20 |
| DE60305459T2 (de) | 2006-11-09 |
| CA2480337C (en) | 2012-05-01 |
| DE10246770A1 (de) | 2003-10-16 |
| CN1323610C (zh) | 2007-07-04 |
| AU2003218777A1 (en) | 2003-10-08 |
| DE60305459D1 (de) | 2006-06-29 |
| ITMI20020632A0 (it) | 2002-03-27 |
| RU2304886C2 (ru) | 2007-08-27 |
| WO2003079816A1 (en) | 2003-10-02 |
| AU2003218777B2 (en) | 2009-10-08 |
| NO326876B1 (no) | 2009-03-09 |
| JP4276088B2 (ja) | 2009-06-10 |
| EP1487282A1 (de) | 2004-12-22 |
| NO20044021L (no) | 2004-11-08 |
| IL164253A0 (en) | 2005-12-18 |
| JP2005520532A (ja) | 2005-07-14 |
| CA2480337A1 (en) | 2003-10-02 |
| US20050153038A1 (en) | 2005-07-14 |
| HK1075182A1 (en) | 2005-12-09 |
| ES2263961T3 (es) | 2006-12-16 |
| PT1487282E (pt) | 2006-07-31 |
| KR101037271B1 (ko) | 2011-05-26 |
| ATE326865T1 (de) | 2006-06-15 |
| ITMI20020632A1 (it) | 2003-09-29 |
| CN1642443A (zh) | 2005-07-20 |
| EP1487282B1 (de) | 2006-05-24 |
| KR20040101316A (ko) | 2004-12-02 |
| PL203697B1 (pl) | 2009-11-30 |
| DK1487282T3 (da) | 2006-09-25 |
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